(1'S,3'R,4'R,5'R,7'S)-N²-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine

Base Information

• Chemical Name: (1'S,3'R,4'R,5'R,7'S)-N²-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine
• CAS No.: 389633-41-4
• Molecular Formula: C₄₀H₄₅N₅O₇Si
• Molecular Weight: 735.912
• Mol file: 389633-41-4.mol

Synonyms:(1'S,3'R,4'R,5'R,7'S)-N²-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine

Chemical Property of (1'S,3'R,4'R,5'R,7'S)-N²-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,3'R,4'R,5'R,7'S)-N²-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine

There total 14 articles about (1'S,3'R,4'R,5'R,7'S)-N²-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

1,7-dihydro-2-(isobutyroyl)amino-6H-purin-6-one (21047-89-2) + (1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane (389633-40-3) → (1'S,3'R,4'R,5'R,7'R)-N2-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine (389633-43-6) + (1'S,3'R,4'R,5'R,7'S)-N2-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine (389633-41-4) + (1'S,3'R,4'R,5'R,7'R)-N2-isobutyryl-7-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine (389633-44-7) + (1'S,3'R,4'R,5'R,7'S)-N2-isobutyryl-7-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine (389633-42-5)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 50 ℃; for 4h;

DOI:10.1021/ja037211z

Reference yield:

(3aS,5R,6R,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3a-phenyl-hexahydro-furo[3,2-b]furan-2,6-diol → (1'S,3'R,4'R,5'R,7'S)-N2-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine (389633-41-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 39 h / 20 °C

2: 15 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 4 h / 50 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1021/ja037211z

Reference yield:

[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetaldehyde → (1'S,3'R,4'R,5'R,7'S)-N2-isobutyryl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}guanine (389633-41-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 269 mg / aq. H₂SO₄ / tetrahydrofuran / 6 h / 60 °C

2: 90 percent / pyridine / 39 h / 20 °C

3: 15 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 4 h / 50 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja037211z

upstream raw materials:

2-N-isobutyrylguanine

(1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane

1,7-dihydro-2-(isobutyroyl)amino-6H-purin-6-one

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

(1'S,3'R,4'R,5'R,7'S)-N²-isobutyryl-9-(4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl)guanine